Choosing this week’s winner was a difficult as balancing a hat on a burro, so we turned to Mary Ryan, who has seen many strange yet historic images from the holdings of the National Archives in her role the managing editor of Prologue magazine.

Congratulations to Kim! Check your e-mail for a code for 15% off in the National Archives eStore.

Our guest judge recognized the setting of this picture from a Prologue article about the Mexican Punitive Expedition, but apparently this beast of burden was not being punished by the Army. The original caption reads “Privates Daly, Ball, and Baldwin, Company A, 16th Infantry, testing out the burro. This burro came to camp one day and ever afterward persisted in hanging around. September 29, 1916. 1922.”

This week’s image features a trio of people, but there are no burros in this one! Just an expression of surprise . . . or shock . . . or arty thoughtfulness. Give us your best caption in the comments below!